Synthesis and characterization of N-(arylcarbamothioyl)- cyclohexanecarboxamide derivatives: The crystal structure of N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide

Article abstract of DOI:10.3390/molecules14020655

A number of N-(arylcarbamothioyl)cyclohexanecarboxamide derivatives (aryl substituents: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, o-tolyl, p-tolyl, 3methoxyphenyl, 4-methoxyphenyl and naphthalen-lyl) have been synthesized. The compounds obta

Full text of DOI:10.3390/molecules14020655

Molecules 2009, 14, 655-666; doi:10.3390/molecules14020655
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molecules
ISSN 1420-3049
www.mdpi.com/journal/molecules
Article
Synthesis and Characterization of N-(Arylcarbamothioyl)-
cyclohexanecarboxamide Derivatives: The Crystal Structure of
N-(Naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide
Cemal Koray Özer 1, Hakan Arslan 1,2,*, Don VanDerveer 3 and Nevzat Külcü 4
1
Department of Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR 33169, Turkey;
2
Department of Natural Sciences, Fayetteville State University, Fayetteville, NC 28301, USA
3
Department of Chemistry, Clemson University, Clemson, SC 29634, USA; E-mail:
dvander@clemson.edu (D. V.)
4
Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343,
Turkey; E-mail: nkulcu@mersin.edu.tr (N. K.)
* Author to whom correspondence should be addressed; E-mails: hakan.arslan.acad@gmail.com or
arslanh@mersin.edu.tr.
Received: 9 January 2009; in revised form: 21 January 2009 / Accepted: 5 February 2009 /
Published: 10 February 2009
Abstract: A number of N-(arylcarbamothioyl)cyclohexanecarboxamide derivatives (aryl
substituents: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, o-tolyl, p-tolyl, 3-
methoxyphenyl, 4-methoxyphenyl and naphthalen-1yl) have been synthesized. The
1
compounds obtained were characterized by elemental analyses, IR spectroscopy and H-
NMR spectroscopy. N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide, H2L9,
was also characterized by a single crystal X-ray diffraction study. This compound,
C18H20N2OS, crystallizes in the triclinic space group Pī, with Z = 2, and unit cell
parameters a = 6.9921(14) Å, b = 11.002(2) Å, c = 12.381(3) Å, α = 113.28(3)°, β =
99.38(3)°, and γ = 101.85(3)°. The cyclohexane ring adopts a chair conformation. The
molecular conformation of the compound is stabilized by an intramolecular (N2-H2•••O1)
hydrogen bond which forms a pseudo-six-membered ring.
Keywords: Synthesis; Cyclohexane; Thiourea; Single crystal structure; Pseudo-six-
membered ring.

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656
Introduction
Chelating extractants have been found to be more selective for separating metal ions than solvating
reagents and anion exchangers. Some of the most important chelating extractants are thiourea
derivatives, which have been known for a long time and are easily synthesized in good yields. Metal
complexes of thiourea derivatives have been the subject of considerable study [1-13]. The presence of
hard O- and N- and soft S-donor atoms in the backbones of these ligands enable them to react readily
with both transition group and main group metal ions, yielding stable metal complexes, some of which
have been shown to exhibit interesting physico-chemical properties and significant biological activities
[13-15]. They have received particular attention because of their potential use as highly selective
reagents for the pre-concentration and separation of metals [16-20]. Some thiourea derivatives have
been found to be useful as insecticides, fungicides, herbicides, and plant-growth regulators
[13,14,21,22]. In recent years, thiourea derivatives have been the subject of interest because it has been
shown that they have antitumor and antifungal bioactivities and inhibitory activities against viruses
[15,23,24].
Over the past couple of years we have been focusing on the preparation and characterization of new
carboxamides which are bonded with a thiourea group [1-5,25-32]. Taking into consideration all the
features described above, we focused our efforts in the present work on the synthesis of carboxamide
derivatives. We have now obtained nine novel carboxamide derivatives and, in this paper, we report
the preparation and characterization of these new derivatives: N-(phenylcarbamothioyl)
cyclohexanecarboxamide (H2L1), N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide (H2L2),
N-(3-chlorophenylcarbamothioyl)cyclohexanecarboxamide (H2L3), N-(4-chlorophenylcarbamothioyl)
cyclohexanecarboxamide (H2L4), N-(o-tolylcarbamothioyl)cyclohexanecarboxamide (H2L5), N-(p-
tolylcarbamothioyl)cyclohexanecarboxamide (H2L6), N-(3-methoxyphenylcarbamothioyl)cyclohexane
carboxamide (H2L7), N-(4-methoxyphenylcarbamothioyl)cyclohexanecarboxamide (H2L8) and N-
(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide (H2L9). The crystal structure of the last
compound is also described.
Results and Discussion
The synthesis of intermediate and target compounds were performed as illustrated in Figure 1. The
derivatives were synthesized in excellent yields following the method described by Douglass and
Dains [33], which involved the reaction of a cyclohexanecarbonyl chloride with potassium thiocyanate
in acetone followed by condensation of the resulting cyclohexanecarbonyl isothiocyanate with the
appropriate primary amine. All spectroscopic methods and elemental analyses confirm the proposed
structures of the new compounds.
The characteristic IR bands of the synthesized compounds are presented in the Experimental
section. The compounds showed two peaks in the 3256-3227 cm-1 and 3215-3134 cm-1 regions due to
the N-H stretching vibrations. This difference between the νNH stretching vibration frequencies is due
to an intramolecular hydrogen bond (X-ray single crystal diffraction data), whereby the carbonyl group
is connected to the imine group. Compounds showed a single peak in the 1690-1682 cm-1 region,
which was due to the C=O stretching vibration. A strong band in the 1252-1238 cm-1 region is

Molecules 2009, 14
657
assigned as the thiocarbonyl group stretching vibration band. These results agree with the literature
data [1-5,25,26,33-35].
Figure 1. Syntheses of the compounds.
O
Cl
O
S
O
S
N
H
N
H
N
H
N
H
+ KSCN
- KCI
H2L9
NH2
H2L1
NH2
O
S
OCH3
O
S
H2N
Cl
NH2
N
H
N
H
N
H
N
H
Cl
O
OCH3
H2L2
H2L8
N C
S
NH2
OCH3
Cl
NH2
O
S
O
S
N
H
N
H
Cl
NH2
NH2
CH3
Cl
N
H
N
H
OCH3
H3C
H2L3
NH2
H2L7
Cl
CH3
O
S
O
S
O
S
N
N
H
N
H
N
H
H
N
H
N
H
H2L4
CH3
H2L6
H2L5
1
1
The H-NMR data of the compounds are presented in the Experimental section. The H-NMR
spectra of the compounds are consistent with the structural results. We discuss only the N-H signal of
the investigated compounds. The two N-H signals for the compounds are observed in the 12.15-12.62
ppm region and in the 8.76-9.21 ppm range. Because of the formation of an intramolecular hydrogen
bond, the imine group proton participating in the hydrogen bond appears at low field [34]. The other
imine proton appears at high field. This data agrees with the results of Li et al. and Mansuroglu et al.
[26, 35]. All of these data agree with FT-IR ATR and X-ray single crystal diffraction results.
The structure of N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide was confirmed by the
result of a single crystal X-ray structure determination. Experimental details for data collection and
structure refinement are summarized in Table 1. An ORTEP diagram of the molecular structure of
H2L9 in the crystal form with the corresponding atom numbering scheme is shown in Figure 2.
Selected bond lengths and angles can be found in Table 2. The bond lengths of the carbonyl (C12-O1
= 1.218(5) Å) and thiocarbonyl (C11-S1 = 1.670(4) Å) groups of the N-(naphthalen-1-
ylcarbamothioyl)-cyclohexane carboxamide have typical double-bond character [36-40]. However, the

Molecules 2009, 14
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C-N bond lengths for the investigated compound are all shorter than the average single C-N bond
length of 1.48 Å, being C12-N1 = 1.388(5) Å, C11-N1= 1.378(5) Å, C11-N2 = 1.340(6) Å, thus
showing varying degrees of double bond character [22, 39-44]. These results are in agreement with the
expected delocalization in N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide and confirmed
by C11-N1-C12 = 129.7(4)o and C11-N2-C1 = 122.1(4)o angles showing an sp2 hybridization on the
N1 and N2 atoms. As presented in Figure 2, the molecule maintains its cis-trans configuration with
respect to the position of the naphthalene and cyclohexane groups relative to the thiocarbonyl sulfur
atom across the N1-C11 and N2-C11 bonds, respectively [42-44].
Table 1. Summary of crystallographic data and parameters of N-(naphthalen-1-
ylcarbamothioyl)cyclohexanecarboxamide.
Empirical formula
Formula weight
Temperature (K)
Wavelength (Å)
Crystal system
Space group
Unit cell dimensions
a (Å)
C18H20N2OS
312.42
153(2)
0.71073
Triclinic
Pī
6.9921(14)
11.002(2)
12.381(3)
113.28(3)
99.38(3)
101.85(3)
824.1(3)
2
b (Å)
c (Å)
α (°)
β (°)
γ (°)
3
V (Å )
Z
Dc (Mg/m3)
1.259
Absorption coefficient (mm-1)
0.200
F(000)
332
Crystal size (mm3)
θ range for data collection (°)
0.29 x 0.24 x 0.14
3.37 to 25.05
-8 ≤ h ≤ 8
Index ranges
-10 ≤ k ≤ 13
-14 ≤ l ≤ 14
Reflections collected
Independent reflections (Rint)
Absorption correction
Refinement method
5439
2841 (0.0261)
Semi-empirical from equivalents
Full-matrix least-squares on F
2841 / 199
2
Data / parameters
2
Goodness-of-fit on F
1.104
Final R indices [I>2σ(I)]
R1 = 0.0884, wR2 = 0.2414
R indices (all data)
Largest diff. peak and hole (e.Å ) 1.208 and -0.578
R1 = 0.1236, wR2 = 0.2990
-3

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659
Figure 2. Molecular structure of H2L9. Thermal ellipsoids are shown at the 50% probability level.
Table 2. Selected bond lengths (Å) and angles (o).
Bond lengths
O1-C12
S1-C11
N1-C12
N1-C11
1.218(5)
1.670(4)
1.388(5)
1.378(5)
N2-C11
N2-C1
1.340(6)
1.466(6)
1.504(6)
C12-C13
Bond angles
C12-N1-C11
C11-N2-C1
N1-C11-N2
N2-C11-S1
129.7(4)
122.1(4)
116.3(4)
123.8(3)
N1-C11-S1
O1-C12-N1
O1-C12-C13
N1-C12-C13
119.8(3)
121.7(4)
124.2(4)
114.0(3)
The conformation of the H2L9 molecule with respect to the thiocarbonyl and carbonyl moieties is
twisted, as reflected by the torsion angles O1-C12-N1-C11, C12-N1-C11-N2, and S1-C11-N1-C12 of -
1.23o, 6.42o and 176.83o, respectively. The O1-C12-N1-C11-N2 plane has a maximum deviation of
0.038(4) Å for C11 atom. However, the central carbonyl thiourea moiety (S1-C11-N2-N1-C12-O1)
connecting the naphthalene and cyclohexane groups is almost planar, with the O1 atom deviating by
0.047(4) Å. In addition, the naphthalene rings are essentially planar. The cyclohexane ring exhibits a
puckered conformation, with puckering parameters [45], q2 = 0.014(6) Å, q3 = -0.572(6) Å, QT =
0.571(6) Å, θ = 180.0(6)o and ϕ = 192(23)o. The largest deviations from the mean plane are 0.241(5) Å
for atom C13 and 0.225(6) Å for atom C16. This ring puckering analysis shows that the cyclohexane
ring has a chair conformation, with equatorial substitution at C13 for C12. In the crystal structure, the
molecules are packed as dimers, via intermolecular contacts N1-H1•••S1i, with N-H 0.91 Å, H-S 2.48
Å, N-H•••S 172o and N2-H2•••O1ii, with N-H 0.91 Å, H-O 2.48 Å, N-H•••O 139o symmetry code: (i) -
3-x, 1-y, -1-z; (ii) -3-x, -y, -1-z as shown in Figure 3. The intramolecular hydrogen bonding N2-
H2•••O1 maintains the six-membered ring formation of the O1-C12-N1-C11-N2 plane; N2-H2•••O1

Molecules 2009, 14
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with N-H 0.91 Å, H•••O 1.98 Å, N-H•••O 132o (Figure 3). The bond distances and angles observed in
the H2L9 molecule is consistent with those reported for the other similar thiourea derivative [25]. It
appears that this intramolecular hydrogen bonding is also present in the solution state. We base this
conclusion on both the IR and NMR evidence cited above and the coordination behavior of the
investigated compound. These thiourea derivatives have one imine group like N,N-dialkyl-N’-
benzoylthioureas [1-5]. These compounds easily coordinate to a metal atom via both sulfur and oxygen
atoms. However, for the title type thiourea compounds [R(Ar)-CO-NH-CS-NH-R(Ar)] we observe that
the carbonyl oxygen atom of the thiourea derivatives does not participate in the coordination with
transition metal atoms because of the strong N-H•••O intramolecular hydrogen bond [26].
Figure 3. Packing diagram for H2L9 with hydrogen bonds as dotted lines [46].
Experimental
General
All chemicals used for the preparation of the compounds were of reagent grade quality. The room
temperature attenuated total reflection Fourier transform infrared (FT-IR ATR) spectra of the all
synthesized compounds were registered using a Varian FTS1000 FT-IR spectrometer with a

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1
Diamond/ZnSe prism (4000–525 cm−1; number of scans: 250; resolution: 1 cm−1). All H-NMR
spectra were recorded on a Bruker DPX-400 spectrometer, using CDCl3 as the solvent and TMS as an
internal standard. C, H and N analyses were carried out on a Carlo Erba MOD 1106 elemental
analyzer. Single crystal X-ray data were collected on a Rigaku Mercury AFC8S system with a
Mercury CCD detector using graphite-monochromated MoKα radiation (λ = 0.71073 Å). The structure
was solved by direct methods and refined by using full-matrix least-squares techniques (on F2) [47].
Data were corrected for Lorentz and polarization effects and for absorption. The latter correction was
made using REQABA, a multi-scan technique [48]. All non-hydrogen atoms were refined
anisotropically. Further details concerning data collection and refinement are given in Table 1.
Synthesis of the compounds
The compounds were prepared by a procedure similar to that reported in the literature [1-5, 22]. A
solution of cyclohexanecarbonyl chloride (0.005 mole) in acetone (50 mL) was added dropwise to a
suspension of potassium thiocyanate (0.005 mole) in acetone (50 mL). The reaction mixture was
heated under reflux for 30 min, and then cooled to room temperature. A solution of the appropriate
primary amine (0.005 mole) (2-chlorobenzenamine, 3-chlorobenzenamine, 4-chlorobenzenamine, o-
toluidine, p-toluidine, 3-methoxybenzenamine, 4-methoxybenzenamine, and naphthalen-1-amine) in
acetone (30 mL) was added to the mixture for 15 min at room temperature and stirred for 2 h.
Hydrochloric acid (0.1 N, 300 mL) was added and the solution was filtered. The solid product was
washed with water and purified by recrystallization from an ethanol-dichloromethane mixture (1:2).
o
N-(phenylcarbamothioyl)cyclohexanecarboxamide (H2L1): White. Yield: 91 %. M.p.: 162-164 C.
Anal. calcd. for C14H18N2OS: C 64.1; H 6.9; N 10.7. Found: C 64.3; H 7.0; N 10.6 %. FT-IR (cm-1):
ν(NH) 3244, 3151 (m), ν(Ar-CH) 3065, 3034 (w), ν(CH) 2933, 2859 (s), ν(C=O) 1686 (s), ν(C=S)
1246 (s). 1H-NMR: δ 12.48 (s, 1H, CSNH), 8.97 (s, 1H, CONH), 7.67 (d, 2H, Ar-H), 7.42 (t, 2H, Ar-
H), 7.28 (t, 1H, Ar-H), 2.30 (tt, J = 10.1, 3.2, 1H, CH, cyclohexane:Ch), 1.99 (d, J = 2.1, 1H, CH,
Ch), 1.94 (d, J = 2.0, 1H, CH, Ch), 1.88 (m, 1H, CH, Ch), 1.84 (t, J = 1.9, 1H, CH, Ch), 1.73 (m, 2H,
CH, Ch), 1.52 (m, 2H, CH, Ch), 1.31 (m, 2H, CH, Ch).
N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide (H2L2): White. Yield: 93 %. M.p.: 136-
o
138 C. Anal. calcd. for C14H17N2OSCI: C 56.7; H 5.8; N 9.4. Found: C 55.9; H 5.7; N 9.6 %. FT-IR
(cm-1): ν(NH) 3227, 3197 (m), ν(Ar-CH) 3097, 3035, 2995 (vw), ν(CH) 2937, 2926, 2854 (m), ν(C=O)
1686 (s), ν(C=S) 1246 (s). 1H-NMR: δ 12.60 (s, 1H, CSNH), 8.76 (s, 1H, CONH), 7.49 (d, 1H, Ar-H),
7.46 (d, 1H, Ar-H), 7.34 (td, 1H, Ar-H), 7.23 (td, 1H, Ar-H), 2.29 (tt, J = 10.3, 3.6, 1H, CH, Ch), 2.01
(d, J = 2.3, 1H, CH, Ch), 1.97 (d, J = 2.2, 1H, CH, Ch), 1.89 (t, J = 2.1, 1H, CH, Ch), 1.85 (m, 1H,
CH, Ch), 1.73 (m, 2H, CH, Ch), 1.55 (m, 2H, CH, Ch), 1.31 (m, 2H, CH, Ch).
N-(3-chlorophenylcarbamothioyl)cyclohexanecarboxamide (H2L3): White. Yield: 89 %. M.p.: 163-
o
165 C. Anal. calcd. for C14H17N2OSCI: C 56.7; H 5.8; N 9.4. Found: C 57.6; H 5.8; N 9.5 %. FT-IR
(cm-1): ν(NH) 3242, 3134 (m), ν(Ar-CH) 3064, 3026 (vw), ν(CH) 2937, 2929, 2852 (m), ν(C=O) 1688
(vs), ν(C=S) 1240 (s). 1H-NMR: δ 12.56 (s, 1H, CSNH), 9.07 (s, 1H, CONH), 7.82 (t, 1H, Ar-H), 7.53

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(dt, 1H, Ar-H), 7.34 (t, 1H, Ar-H), 7.25 (dt, 1H, Ar-H), 2.30 (tt, J = 10.7, 3.8, 1H, CH, Ch), 1.97 (d, J
= 2.4, 1H, CH, Ch), 1.93 (d, J = 2.2, 1H, CH, Ch), 1.87 (t, J = 2.2, 1H, CH, Ch), 1.83 (m, 1H, CH,
Ch), 1.74 (m, 2H, CH, Ch), 1.51 (m, 2H, CH, Ch), 1.31 (m, 2H, CH, Ch).
N-(4-chlorophenylcarbamothioyl)cyclohexanecarboxamide (H2L4): White. Yield: 86 %. M.p.: 184-
o
186 C. Anal. calcd. for C14H17N2OSCI: C 56.7; H 5.8; N 9.4. Found: C 56.6; H 5.9; N 9.6 %. FT-IR
(cm-1): ν(NH) 3254, 3153 (m), ν(Ar-CH) 3066, 3034 (w), ν(CH) 2941, 2924, 2858 (m), ν(C=O) 1686
(vs), ν(C=S) 1252 (s). 1H-NMR: δ 12.51 (s, 1H, CSNH), 9.01 (s, 1H, CONH), 7.63 (d, 2H, Ar-H), 7.38
(d, 2H, Ar-H), 2.29 (tt, J = 10.4, 3.5, 1H, CH, Ch), 1.97 (s, 1H, CH, Ch), 1.93 (s, 1H, CH, Ch), 1.87
(d, J = 2.1, 1H, CH, Ch), 1.84 (d, J = 2.3, 1H, CH, Ch), 1.75 (m, 2H, CH, Ch), 1.51 (m, 2H, CH, Ch),
1.30 (m, 2H, CH, Ch).
o
N-(o-tolylcarbamothioyl)cyclohexanecarboxamide (H2L5): White. Yield: 91 %. M.p.: 148-150 C.
Anal. calcd. for C15H20N2OS: C 65.2; H 7.3; N 10.1. Found: C 65.8; H 7.4; N 10.3 %. FT-IR (cm-1):
ν(NH) 3236, 3165 (m), ν(Ar-CH) 3065, 3028 (w), ν(CH) 2932, 2853 (m), ν(C=O) 1686 (s), ν(C=S)
1246 (m). 1H-NMR: δ 12.15 (s, 1H, CSNH), 9.16 (s, 1H, CONH), 7.72 (dd, 1H, Ar-H), 7.31-7.22 (m,
3H, Ar-H), 2.34 (s, 3H, Ar-CH3), 2.32 (tt, J = 10.3, 3.3, 1H, CH, Ch), 2.00 (d, J = 2.4, 1H, CH, Ch),
1.95 (s, 1H, CH, Ch), 1.87 (m, 1H, CH, Ch), 1.83 (m, 1H, CH, Ch), 1.74 (m, 2H, CH, Ch), 1.52 (m,
2H, CH, Ch), 1.30 (m, 2H, CH, Ch).
o
N-(p-tolylcarbamothioyl)cyclohexanecarboxamide (H2L6): White. Yield: 90 %. M.p.: 176-178 C.
Anal. calcd. for C15H20N2OS: C 65.2; H 7.3; N 10.1. Found: C 66.0; H 7.3; N 10.3 %. FT-IR (cm-1):
ν(NH) 3240, 3172 (m), ν(Ar-CH) 3034 (w), ν(CH) 2932, 2859 (m), ν(C=O) 1686 (s), ν(C=S) 1250 (s).
1H-NMR: δ 12.38 (s, 1H, CSNH), 8.98 (s, 1H, CONH), 7.52 (d, 2H, Ar-H), 7.22 (d, 2H, Ar-H), 2.38
(s, 3H, Ar-CH3), 2.29 (tt, J = 10.2, 3.7, 1H, CH, Ch), 1.98 (s, 1H, CH, Ch), 1.94 (s, 1H, CH, Ch), 1.87
(m, 1H, CH, Ch), 1.83 (m, 1H, CH, Ch), 1.74 (m, 2H, CH, Ch), 1.51 (m, 2H, CH, Ch), 1.31 (m, 2H,
CH, Ch).
N-(3-methoxyphenylcarbamothioyl)cyclohexanecarboxamide (H2L7): White. Yield: 93 %. M.p.: 94-96
oC. Anal. calcd. for C15H20N2O2S: C 61.6; H 6.9; N 9.6. Found: C 62.5; H 6.8; N 9.6 %. FT-IR (cm-1):
ν(NH) 3256, 3215 (m), ν(Ar-CH) 3034, 3005 (w), ν(CH) 2943, 2939, 2916, 2862, 2849, 2841 (m),
ν(C=O) 1690 (s), ν(C=S) 1246 (s). 1H-NMR: δ 12.53 (s, 1H, CSNH), 9.08 (s, 1H, CONH), 7.44 (t, 1H,
Ar-H), 7.30 (d, 1H, Ar-H), 7.18 (dd, 1H, Ar-H), 6.83 (dd, 1H, Ar-H), 3.83 (s, 3H, OCH3), 2.30 (tt, J =
10.3, 3.2, 1H, CH, Ch), 1.98 (d, J = 2.5, 1H, CH, Ch), 1.93 (d, J = 2.4, 1H, CH, Ch), 1.86 (m, 1H, CH,
Ch), 1.83 (m, 1H, CH, Ch), 1.73 (m, 2H, CH, Ch), 1.51 (m, 2H, CH, Ch), 1.30 (m, 2H, CH, Ch).
N-(4-methoxyphenylcarbamothioyl)cyclohexanecarboxamide (H2L8): White. Yield: 94 %. M.p.: 167-
o
169 C. Anal. calcd. for C15H20N2O2S: C 61.6; H 6.9; N 9.6. Found: C 61.3; H 6.8; N 9.4 %. FT-IR
(cm-1): ν(NH) 3236, 3202 (m), ν(Ar-CH) 3041, 3013 (w), ν(CH) 2934, 2928, 2850, 2843 (m), ν(C=O)
1686 (s), ν(C=S) 1238 (s). 1H-NMR: δ 12.29 (s, 1H, CSNH), 8.93 (s, 1H, CONH), 7.53 (dt, 2H, Ar-H),
6.94 (dt, 2H, Ar-H), 3.84 (s, 3H, OCH3), 2.28 (tt, J = 10.4, 3.4, 1H, CH, Ch), 1.98 (d, J = 2.4, 1H,

Molecules 2009, 14
663
CH, Ch), 1.93 (d, J = 2.4, 1H, CH, Ch), 1.87 (m, 1H, CH, Ch), 1.83 (m, 1H, CH, Ch), 1.74 (m, 2H,
CH, Ch), 1.51 (m, 2H, CH, Ch), 1.30 (m, 2H, CH, Ch).
N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide (H2L9): White. Yield: 92 %. M.p.: 176-
178 oC. Anal. calcd. for C18H20N2OS: C 69.2; H 6.5; N 9.0. Found: C 69.9; H 6.4; N 8.9 %. FT-IR (cm-
1): ν(NH) 3233, 3169 (m), ν(Ar-CH) 3051, 3030 (w), ν(CH) 2932, 2922, 2852 (m), ν(C=O) 1682 (s),
1
ν(C=S) 1242 (m). H-NMR: δ 12.62 (s, 1H, CSNH), 9.21 (s, 1H, CONH), 7.98-7.81 (m, 4H, Ar-H),
7.58-7.48 (m, 3H, Ar-H), 2.30 (tt, J = 10.2, 3.3, 1H, CH, Ch), 1.98 (s, 1H, CH, Ch), 1.94 (s, 1H, CH,
Ch), 1.83 (d, J = 2.3, 1H, CH, Ch), 1.79 (d, J = 2.2, 1H, CH, Ch), 1.69 (m, 2H, CH, Ch), 1.52 (m, 2H,
CH, Ch), 1.25 (m, 2H, CH, Ch).
Supplementary material
Crystallographic data for the structure reported in this paper have been deposited at the Cambridge
Crystallographic Data Centre (CCDC) with quotation number CCDC-675756 for H2L9 and can be
obtained free of charge on application to CCDC 12 Union Road, Cambridge CB2 1EZ, UK Fax:
(internat.) + 44(1223)336-033, E-mail: deposit@ccdc.cam.ac.uk.
Acknowledgements
Support for this research was provided by grant P20 MD001089 and S06 GM078246-01 from the
USA National Institution of Health, NCMHD, and Department of Health and Human Services and by
grant BAP.ECZ.F.TB.(HA).2007-1 from Mersin University Research Fund.
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